Water-insoluble mono-azo-dye-stuffs and fiber dyed therewith



Patented June 5, 1934 UNITED STATES PATENT OFFIE WATER INSOLUBLE MONOAZO DYE- STUFFS AND FIBER DYED THEREWITH tion of Delaware No Drawing.Application July 10, 1933, Serial No. 679,826. In Germany July 30, 19324 Claims.

0 OHa-CHz-O R on, o marred-o CHa wherein R means alkyl.

These dyestuffs may be obtained by coupling the diazo compounds of1-amino-2 -alkoxy-2- ethoxy--nitrobenzenes of the followingconstitution:

30, wherein R means alkyl, with 2'-hydroxynaphthalene 3 carbonyl(1-amino-4-methoxy3 methylbenzene), either in substance, on the fiber oran any of the usual substrata adapted for the production of lakes.

There are thus obtained Bordeaux red monoazo-dyestufis which aredistinguished by good fastness properties, especially by a very goodfastness to exposure. In this respect, they surpass by far thecombination prepared from diazotized 5-nitro-2-anisidine and2-hydroxynaphthalene- 3 carbonyl (1 amino-,4-methoxy-3-methylbenzene),described in French Patent No. 679,280.

The said nitro bodies may be prepared, for instance, from2-aminophenylglycolalkylethers by nitrating the correspondingbenzenesulfarnides which may be obtained by condensing the aminocompoundwith benzenesulfochloride.

The following examples serve to illustrate the invention, but they arenot intended to limit it thereto, the parts being by weight unlessstated otherwise; the relationship between parts by weight and parts byvolume is that which exists between a kilogram and a liter:

1. A paste is prepared in a finely dispersed form from 27.4 parts ofl-amino-fi-methoxy-Z- ethoxy-4-nitrobenzene, parts by volume ofhydrochloric acid of 20 B. and a small quantity of cold water and it isdiazotized by addition of 7 parts of sodium nitrite in an aqueoussolution at a temperature of 5 C. to 10 C. The diazo solution is thencoupled with a solution of 32.2 parts of2-hydroxy-naphthalene3-carbony1- (l-amino-4-methoxy-3-methylbenzene) indilute caustic soda solution to which there have been added the quantityof sodium acetate necessary for binding the excess of mineral acid, andTurkey red oil, and, at the same time, part of the acetic acid isneutralized by gradually adding sodium bicarbonate solution. Theprecipitated dyestuff which corresponds to the following formula:

is filtered with suction and washed well. When mixed in the usual mannerwith substrata, it yields a Bordeaux red lake of very good fastness tolight.

2. In order to prepare the dyestuff on the fiber, cotton material whichhas been pretreated in the usual manner, is impregnated in a solutionwhich contains per liter:

5.5 parts of 2-hydroxynaphtha1ene-3'-carbonyl(1-amino4-methoxy 3methylbenzene) 11 parts by volume of caustic soda solution of 34 B. and10 parts by volume of Turkey red oil, the material is well squeezed anddeveloped in a feebly acetic acid solution which contains per liter:

2.75 parts of l-amino-2 -rnethoxy-2-ethoxyl-nitrobenzene, it is rinsedand soaped.

A Bordeaux red dyeing of very good fastness to exposure is thusobtained.

By replacing in the foregoing example 2.75 parts of 1-amino-2-methoxy-2-ethoxy-a-nitrobenzene by the corresponding quantity ofl-amino-2 -ethoxy2-ethoxy-4-nitrobenzene, there is likewise obtained aBordeaux red dyeing. By using the diazc compound froml-amino-22-nbutoxy-2-ethoxy-4-nitrobenzene, a dark Bordeaux red dyeingis obtained.

The dyestuffs may also be prepared on the fiber according to one of theusual printing processes.

We claim:

1. Water-insoluble mono-azo-dyestuffs of the following general formula:

wherein R, means alkyl, dyeing Bordeaux red shades of good fastnessproperties, particularly of very good fastness to exposure.

2. The water-insoluble mono-azo-dyestuff of the following formula:

LEOPOLD LASKA.

ARTHUR ZITSCHER.

